


Last Stop Oneshots

by crazyassCas



Category: Supernatural
Genre: M/M
Language: English
Status: In-Progress
Published: 2016-12-24
Updated: 2017-01-02
Packaged: 2018-09-11 15:10:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 9,317
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8992807
Author URL: https://archiveofourown.org/users/crazyassCas/pseuds/crazyassCas
Summary: A compilation of oneshots set in the Last Stop on the H Train AU. They probably won't make any sense unless you read the main story.Each chapter will have its own summaries and warnings.





	1. Chapter 1

**Summary for the Chapter:**

> This oneshot takes place four years after Dean and Cas got clean.
> 
> TRIGGER WARNING: mentions of rape

Dean dropped the hood and checked his watch. Bobby had some paperwork to do in his office, and Dean needed to get some work done on the Impala, so Bobby had let him stay late to work on her. It was getting late, and he had just finished up, lowered the lift, and checked her over. He went into the lobby to grab himself a cup of coffee from the machine for the ride home, when the voice from the TV mounted on the wall caught his attention.

He turned around, and his blood ran cold when he saw Al being escorted to a police vehicle in handcuffs.

"Again," the newscaster repeated, "We are showing you footage of Alan Stair, convicted murderer, leaving the courtroom today after being sentenced to life in prison without the possibility of parole. Stair was brought in for questioning last year after state police received an anonymous tip that he was procuring prostitution. After finding DNA evidence in the trunk of his vehicle, which matched missing Oklahoma teen Darius Ramirez, Stair then confessed to over a dozen other murders taking place between-"

Dean's jaw dropped and the cup he was holding fell from his hand, hitting the floor and sending hot coffee flying everywhere. He turned and ran back out to the bay, practically tossing himself into the car and fumbling with the keys. He didn't even say goodbye to Bobby. He jammed the keys into the ignition and peeled out of the garage, pulling out onto the street and pressing down on the gas.

Twelve people. Al had confessed to killing over twelve people, and nearly five years ago, he was almost one of them. His stomach churned and he had to pull over onto the side of the road because he felt like he was going to throw up. His hands shaking, he flung the car door open before lurching forward and vomiting his lunch out onto the road.

Fucking christ, how many of those were in the last five years? How many of those people could Dean have saved if he'd just said something? An anonymous tip had led to Al finally being arrested. If Dean could have been stronger, he could have marched down to the police station and given them Al's first name, and the make and model of his car. Hell, maybe back then he even could've remembered some of his license plate. If he just hadn't been so _weak_ , if he'd been thinking about anybody but himself, maybe he could have saved some of those people.

Everything he'd endured at the hands of Al came flooding back to him. He felt even worse knowing he'd only spent three weeks with him. How long had some of these other people endured his abuse before he finally snapped and killed them? Was he the only one who had survived?

A car swerved by and honked, so he reached out and slammed his door closed again. He crossed his arms over the steering wheel and lowered his head into them, tears streaming down his face. Why was he so fucking selfish? He should've gone to the police. Their deaths were on his head.

He brought a shaking hand to the shifter and dropped it down into drive, pulling back out onto the road and wiping his face. His hands were rough from working on vehicles, and his cheeks stung as he dragged the callouses across his skin. He started back home, slamming on the brakes and taking a sharp right into the parking lot of the town's small strip mall. He quickly parked the Impala and took a deep breath, willing himself to calm down before going out in public. He could only wait two minutes before his feet were carrying him into the liquor store. He grabbed a bottle of Jack off the shelf, brought it up to the register, and reached for his wallet.

"I.D.," the cashier drawled.

He pulled out his ID and slapped it on the counter. She leaned forward to look at it before leaning back and ringing up the bottle.

He snatched it back up and tried to shove it back into the clear pocket, but his hands were trembling. He ended up just tucking it into the back part with his cash. He slid his debit card out of another slot and inserted it into the machine. After a moment, it asked for his pin number, and he quickly punched it in. Then the machine beeped, signaling it had successfully read the chip, so he yanked it back out and shoved it in with his ID.

The cashier bagged his bottle. "Have a nice night," she said tiredly.

He grabbed the bottle and turned without a word, hurrying across the store, out the door, and back into his car. As soon as the door closed behind him, he pulled the bottle out of the brown paper bag, staring down at it and running his thumb over the label.

He was a little over four years sober, but that was ending tonight.

He cracked the bottle open and brought it to his lips, tilting his head back and taking a long swig. He scrunched his eyes shut at the burn in his throat. He didn't even care if he was arrested for drinking in public. At least he couldn't do anything stupid sitting in a jail cell all night. He re-capped the bottle and dropped it onto the seat next to him. He lit a cigarette, started the car, and pulled out of the spot to start the drive home.

By the time he was a mile away from home, he was already starting to feel it. His tolerance certainly wasn't what it used to be. He still couldn't stop thinking about Al though, so as soon as the car lurched to a stop in the driveway, he twisted off the cap and took another swig. As he lowered the bottle and stared at the house through the windshield, he was filled with dread.

He had to go in there and face Cas now, and there was no way in hell Cas wouldn't know he'd been drinking. He lowered his head, his eyes welling up with tears again. Cas was going to be so disappointed.

Four years sober down the drain. He couldn't have waited just one more day? Even 'til morning, or just an hour. Maybe if he'd just waited an _hour_ , he could've calmed down enough to resist.

But he couldn't control himself, and now he'd relapsed; erased four years of sobriety because of a fucking news clip.

He took another gulp of the amber liquid. It burned less now.

Fuck, why did Bobby have to have the news on? He closed his eyes and leaned his head back. It was so much easier to blame somebody else, but _he_ was the one who'd stayed late. If he hadn't planned on staying late, he would've brought Cujo, like he did every other day. If he had just gone home at the end of the workday-

_You can blame it on circumstance all you want. But in the end, it was going to happen anyway. It's because you're weak. Weak, pathetic little Dean Winchester. Could never stand up to your daddy, could never stand up to Al. Sure, you beat some kids up in high school. But when it counts? You run with your tail between your legs._

Fuck. It had been so long since he'd heard that god damn voice, he'd almost forgotten what it sounded like.

Dean took another swig and re-capped the bottle. He took a deep breath, feeling the liquor churning in his stomach and up his esophagus, and pushed open the car door. He slammed it behind him and dragged himself up the driveway. It took him a minute to get his key into the lock, but he finally did, and he pushed the door open, slipping in and closing it behind him.

He didn't see Cas anywhere, but Cujo and Theo immediately ran up to him. Theo jumped on him excitedly but Cujo bean nudging his hands and licking his fingers.

Dean gently swatted his hand to shoo Cujo away. "Go'way, Cujo," he mumbled. It was too late for his help. He might as well take the night off. He took another swig from the bottle, and when he tilted his head forward again and lowered the bottle, Cas was standing in the living room, shock painted on his face.

"Dean-" He rushed across the room towards Dean, his expression changing to worry. "Dean, what happened? Why are you drinking?"

Dean's eyes welled up again, and he started to lift the bottle to his lips again.

Cas reached out and swiftly grabbed the bottle from Dean. "Give me that. Dean, what happened?" he asked, setting the bottle behind him on the kitchen counter.

"They're dead, Cas," he pushed out, his voice cracking. "They're dead an' I coulda stopped it."

Cas' eyebrows knitted together in confusion. "What the hell are you talking about?" He reached out and gently took Dean by both wrists, walking backwards and leading him to the couch. Once they were in front of it, he sat down and tugged Dean to sit down with him.

"Al," Dean said loudly, plopping down on the couch across from Cas. "The guy who fuck- who fuckin raped me," he sobbed.

"Dean, did you see him?" Cas asked quickly.

"No," Dean choked out. "He was- he was on the news. He confessed to murder." He paused. "Twelve people, Cas…"

Dean released Dean's wrists to take his hands in his own. "Dean…"

Dean looked up to meet his eyes. "I coulda saved those people, Cas, if I said somethin'."

Cas looked broken. "Dean, no," he said soothingly. "You can't blame yourself."

Dean took in a shaky breath. _Fuck, you're so whiny and pathetic. It would be funny if it wasn't so sad._ He shook his head. "I coulda stopped him. If… If I'd gone in, made a report, I woulda been evidence-"

"Dean," Cas said sternly. "That doesn't mean anything. He still could've gotten off. There are people serving less than a year for rape. I will not allow you to blame yourself."

"But-"

"No," Cas repeated. He released Dean's hands, bringing his own up to cup the sides of Dean's face. "Look at me."

Dean brought his eyes up to meet Cas'.

"Dean, there is nothing you could have done. You don't know what would have happened if you'd made a report, okay? You could have been poked and prodded after all that trauma, for them to extract a DNA sample, all for nothing. You don't know. And then he could have come looking for you- he had your address. You did what you thought you had to do."

Dean nodded slowly, lowering his gaze to his lap, where Cujo was lying his head on his legs.

Suddenly Dean's face drained of all color and Cas jumped up from the couch. "Stay here." He bolted off into the bathroom, returning with the small waste bin and thrusting it out to Dean, just in time for him to lurch forward and heave into the can.

Dean threw up a decent amount of liquid, most of it whiskey, which made it's way up his nostrils and burned like hell.

"Fuck," he whined. Why did he do this to himself?

Cas reached down and placed his hand on Dean's back, rubbing in small circles. "Get it all out and you'll feel better." He again disappeared into the bathroom. When he returned, he held two hand towels in his hand. He sat back down and pressed one to Dean's forehead. It was soaked in cold water, and it made him feel a little bit better.

He heaved again and what was left of his lunch came up. Cas held the dry towel out and Dean took it from him, bringing it up to his face to wipe his mouth, his other arm holding the waste basket to his chest.

"I'm sorry, Cas," Dean murmured.

"For what?" Cas asked softly.

"Fuckin' up," Dean mumbled, closing his eyes.

"It's okay, Dean," Cas said gently. "It'll be okay. I promise. But you can't do this on the medication that you're on. If you hadn't drank so fast that you threw up right away, I might have had to take you to the hospital."

Dean nodded slowly.

"I don't think you should go out alone without Cujo again, okay?"

Dean nodded again.

Cas stood up and walked over to the kitchen counter, picking up the bottle. "I'm dumping this down the drain."

Dean nodded a third time, causing himself to get dizzy, and he wretched into the can again.

Cas re-appeared next to him, lowering himself onto the couch again and setting his hand on Dean's thigh. "I want you to listen to me, Dean." He paused. "I don't want you to let this set you back. Just because you relapsed and had one bad night doesn't mean you have to throw away all of the progress you've made. ...Okay?"

"Okay," Dean said weakly.

"Would you like to lie down?" Cas asked.

Dean nodded, and Cas took his hand and pulled him up from the couch. Dean followed him into their bedroom, clutching the waste bin to his chest with his other hand. As they neared the bed, Cas took it from him and set it down on the floor.

"Get undressed."

Dean vaguely remembered that he'd just been working all day- his arms and hands were probably covered in grease. "But-"

"It's okay," Cas interrupted. "I'll change the sheets tomorrow. Just get some rest." He smiled warmly. "Tomorrow's a new day."

Dean nodded and undid his jeans, dropping them with his boxers and sitting back on the edge of the bed. He yanked his tee shirt off over his head and dropped it onto the floor with his jeans. "Are you gonna lay with me?"

"It's only nine, but I'll stay in here with you."

"Please," Dean said softly.

Cas nodded and left, momentarily returning with a glass of water. He turned the light off on the way in, then walked around to his side of the bed and clicked on the lamp. Cujo jumped up in the middle of the bed, and as Dean lifted the blanket, Cujo climbed underneath with him. Cas held out the glass of water, and when Dean took it, he settled back into the pillows on his side and picked up his book from his night stand.

Dean took a few sips of water and set the glass down on his night stand. He settled down on his back, turning his head to watch Cas. Although he'd thrown up most of the alcohol, what had made it's way into his system was still there, and he was still buzzed.

Cas' eyes flicked over from his book, and he smiled. "Do you feel a bit better?"

"Yeah," Dean said quietly. "Thank you, Cas."

"Any time, Dean."

"Thank you for always putting me back together. You keep me sane."

Cas smirked. "I'm pretty sure that's the medication."

Dean grinned sleepily. "Yeah, yeah." He paused, staring into Cas' eyes. "I love you."

"I love you, too." Cas leaned down to give him a quick kiss. "Now get some rest."

Dean nodded and shifted onto his side, closing his eyes. As he drifted off to sleep, he expected to have some nightmares, but he had a small smile on his face because he knew Cas and Cujo, like always, would be there to wake him up.


	2. Chapter 2

**Summary for the Chapter:**

> Dean and Cas' first sexual encounter, which Dean promptly forgets in the morning because he was drunk off his ass. Takes place a few months after they first meet.
> 
>  
> 
> Tags: internalized homophobia, smut, frottage, masturbation  
> 6,924 words

"Would you like to come over to my house tonight?" Cas asked casually, holding his burger delicately between his fingers.

Dean glanced up from his own tray, which Cas had been kind enough to purchase for him. "Like, a sleep-over?"

"Yeah," Cas confirmed. "It _is_ your birthday." He took a bite of his cheeseburger.

Dean smiled a little. He'd just turned fifteen, and he'd never been invited to a sleep-over before. He was honestly a little surprised, but it made him happy that this kid seemed to like him so much. "Are your parents okay with it?"

Cas set his burger back down on his tray, chewing and swallowing the bite in his mouth. "They're away."

Dean raised an eyebrow. Was it normal for parents to leave thirteen-year-olds alone? He wouldn't know what normal was, but it seemed a little weird. "Okay. I just don't want you to get in trouble."

Cas smiled a bit. "I won't." Dean nodded. "Can your dad drop you off?"

Dean lowered his eyes. "Um... Where do you live?"

Cas gave him his address and Dean was surprised to realize that Cas only lived a few blocks from him.

"I'll walk," he said, and Cas decided not to ask why. If Dean wanted to walk in January, there had to be a reason.

"Okay. Bring a sleeping bag."

"Oh," Dean said softly, still looking down at his food. "I don't have one."

Cas chewed his lip. He'd never been invited to a sleep-over, so he didn't have one either, or he would've offered for Dean use it. "Oh. Well you can sleep in my bed. Or on the couch."

Dean nodded. "Okay." He picked up a fry and dragged it through his ketchup before shoving it into his mouth. "I probably can't come until late, though. I have to put Sammy to bed."

Cas simply nodded. He knew Dean had to care for his younger brother, but he wasn't sure why. He felt like it wasn't his place to ask. It was a Friday, though, so he supposed it didn't really matter. They could stay up late and sleep in on Saturday.

* * *

That night, Dean put Sam to bed by nine with strict instructions to keep his bedroom door locked and to not open it for anybody but him.

"Where are you going?" his little brother asked.

"I'm going to my friend's house for my birthday," Dean answered, allowing himself a small smile.

Sam's face lit up. "Good. I hope you have fun." He paused, and then he looked a little sad. "I'm sorry I couldn't get you anything."

Dean rolled his eyes. "Stop it, Sammy. You know I don't expect anything." He nodded his head towards Sam's desk, where a bag of chips and a bottle of soda sat on the surface. "Not the best breakfast, but eat that when you wake up, okay? Don't go downstairs, I mean it. When I get home I'll make you something."

Sam nodded. It's not that he was incapable of taking care of himself, he was eleven after all, but he knew Dean didn't like leaving him alone with John. At the moment, he wasn't home, but that could change at any time.

"If he comes home, you shut your light off and you pretend you're not here or something, got it?"

Sam nodded again.

"Okay." He walked over to Sam's desk and pulled out a piece of paper. He pulled another out of his pocket, that Cas had given him, and scribbled the number down onto the new piece of paper. "This is Cas' number. Call it if you need anything, okay? He said I could give it to you." He left the paper on the desk and shoved the other one back into his pocket, walking back towards where Sam was seated on the bed.

Sam nodded a third time, and Dean reached over to ruffle his hair. "Okay, have fun reading your books or whatever the hell it is you do when I'm not around, you nerd."

Sam grinned. "Goodnight, Dean."

"Night, Sammy." He slipped out the door and closed it behind him, pausing and waiting. He heard the lock click and he smiled to himself. Sam was a good kid; a good listener. He snuck into his father's room and snagged a bottle of Jack, tucking it into his jacket and making his way down the stairs. He locked the front door behind him, shoving the key into his jacket pocket and beginning the walk to Cas' house.

As he got closer, he squinted at the numbers on the mailboxes until he got to the one Cas said was his. It was a little bigger than his, but it was way nicer. The paint wasn't dull and peeling and the driveway was actually shoveled as opposed to being packed down and icy. He walked up to the front door and knocked, and a few moments later, Cas opened it.

Dean's eyes widened slightly when Cas answered the door. He'd never seen him in anything but his dress shirt, tie and trench coat, but Cas was now wearing a worn Less Than Jake shirt and jeans. "Um- heya, Cas," he greeted.

"Hello, Dean," Cas said with a smile.

Dean stepped inside and Cas closed the door behind him. Dean pulled his hand out of his jacket, revealing the bottle of Jack. "I come bearing gifts."

Cas snorted. "I'm pretty sure I'm supposed to be the one giving you gifts." He paused, suddenly looking embarrassed. "Although, I didn't get you anything. I have no idea what you like." In his defense, they'd only known each other for three or four months, and they only really got to talk during school.

Dean waved his hand dismissively. "You didn't have to get me anything, man. It's okay. Inviting me over was enough." He dropped his gaze and cleared his throat, and Cas swore he was blushing a bit. "So, um, you ever drank before?" he asked, looking down at the bottle.

"No," Cas admitted sheepishly.

"It's super fun," Dean grinned, returning his eyes to his face and holding up the bottle.

A small smile spread across Cas' lips. "Okay." He glanced behind him, then looked back to Dean. "I'm not sure what you wanted to do, but I have food."

Dean grinned. "Well, I'm not usually one to refuse food, but if I barf later it'll be kind of a mess. Maybe once we start drinking."

Cas nodded. "Do you want to play video games?"

Dean nodded eagerly. "Hell yeah."

Cas smiled again. "Okay." He led Dean upstairs and they sat down on the floor at the foot of the bed. Cas powered up the system and handed Dean a controller.

Dean cracked open the bottle and took a long swig before holding the bottle out to Cas. Cas took it, holding it up to his nose and giving it a cautious sniff.

Dean grinned. "Just drink it. Try not to suck in any air, otherwise it'll burn like hell."

Cas nodded and lifted the bottle to his lips, tilting his head back and taking a small sip. He squeezed his eyes shut and gritted his teeth, gagging a bit as the liquid burned his throat.

"You'll get used to it," Dean chuckled, taking the bottle back and swallowing down another gulp.

They played the game for the next hour or, passing the bottle back and forth, until Dean suddenly flopped backwards to the floor after a rather dramatic on-screen death.

"Are you okay?" Cas asked, leaning forward to peer down at him.

"Mhmm," Dean murmured. Then he started humming.

"What is that?" Cas asked curiously.

"Metallica." He opened one eye to see Cas tilting his head in confusion, and god, it was the most adorable thing he'd ever seen. He propped himself up on his elbows and gave Cas a blank stare. "Okay, you're seriously telling me you've never listened to Metallica?" he asked in disbelief.

Cas shook his head before tilting it back and taking a small sip from the bottle. There was a pleasant warmth radiating out into his limbs, and his head was getting a bit fuzzy. "But I have a laptop. We could play it."

"Yeah," Dean agreed.

Cas reached out and placed his palms on the floor, slowly pushing his legs out from underneath himself and standing up. He carefully made his way to his desk, opening his laptop and loading the internet browser. "What song should I put on?"

"Um..." Dean closed his eyes and trailed off. "Enter Sandman," he decided, re-opening his eyes.

Cas clacked away at his keyboard, swaying a bit where he stood hunched over his desk. He had to re-type it a few times, but eventually he located the song on YouTube.

Dean fund himself drunkenly staring at his ass, and he had to scold himself and look away. Cas was thirteen, and he was fifteen now. He wasn't some kind of pedophile. That aside, he wasn't even _gay_. Yeah, guys were good looking, but that was it. Just because he appreciated the way guys looked didn't make him a homosexual. As the opening chords of the song filled the quiet room, he closed his eyes and nodded his head a bit, humming to himself and trying to clear his thoughts.

Cas straightened up and turned around, plopping back down cross-legged next to Dean. The noise caused Dean to open his eyes, and he took another sip from the bottle before holding it out to Cas. "So, when's your birthday?"

"May twelfth," Cas replied, looking down at the bottle and fiddling with the label.

Okay, so Cas was only four months away from fourteen, so maybe Dean's not a gross pedophile for having a crush on his classmate after all. Wait, what was he thinking? He didn't have a _crush_. Cas was a _boy_.

Only when Cas tipped the bottle to his lips again did Dean realize they'd been quiet for several minutes. "I'm really drunk," he mumbled, pushing himself up a bit and planting his palms on the carpet.

"You've drank quite a bit," Cas agreed. The song ended, and he pushed himself up again to pick something else.

"Did you like it?" Dean asked.

"Yeah, it was okay," Cas said with a nod, squinting at the screen of his laptop. Another song started playing, one Dean didn't recognize. "Now it's my turn to show you a song."

Dean smiled. "Okay." He liked sharing music with Cas. "Hey, let me ask you somethin'," he said nonchalantly, reaching forward to grab the bottle from where Cas left it on the floor.

Cas came and sat back down as Dean swallowed down another drink. "What?"

"You like any of the girls at school?" he asked, passing the bottle back to Cas.

Cas' entire face flushed red, and he looked down at the bottle in his hands, running his thumb over the label. "No." He glanced up. "Why, do you?"

Dean bit his lip into his mouth. "I kinda like that Lisa girl."

"Lisa Braeden?" Cas clarified.

Dean nodded. "Yeah." He paused. "You really don't like anyone?" he asked again, raising an eyebrow.

Cas lowered his eyes to the bottle again and sighed, before lifting it to his lips and tilting his head back. He took a decent gulp, lowering his head again and closing his eyes and gritting his teeth at the burn. When it finally faded, he opened them again, and they were fixed on Dean.

"No," he said again. "I actually, uh..." He worried his bottom lip between his teeth and looked down at the bottle again. Should he tell him? How would Dean react? He really didn't want to lose the only friend he'd made so far in Lawrence, and he really liked Dean. Finally he figured Dean would probably find out soon enough anyway, so he decided to just spit it out. "I don't like girls."

Dean was quiet, and finally Cas glanced up to see him looking at him with an expression he couldn't read, although maybe it was the alcohol making him fuzzy.

"So, like, you're gay?" Dean finally asked.

Cas looked back down at the bottle again. "I guess," he mumbled. It felt like Dean was quiet for hours, although it was probably only a few seconds. "Is that bad?" Cas blurted out, before he could stop himself.

He lifted his eyes and Dean just shrugged his shoulders. "Nah." Then he paused, and his eyebrows pressed together thoughtfully. "Well... my dad says it is. But I think people should do what makes them happy."

Cas swallowed and nodded, looking down at the bottle yet again. "Yeah, I agree."

Dean smirked at him. "Okay, so now that you've told me your big secret, I'll ask again. Anybody you like?"

Cas huffed out a little laugh, his cheeks flushing pink again. "No." He brought the bottle to his lips again, taking another swig. He swore he saw a flicker of disappointment cross Dean's face out of the corner of his eye, but he was positive he was just imagining things. Dean had just made it clear he liked girls; there was no way he would like _Cas_. After he'd swallowed his drink, he looked at Dean again. "So, are you going to ask out Lisa?"

Dean shrugged. "I dunno. I think she's going out with that kid Murphy."

"Oh," Cas said quietly. "I'm sorry."

Dean shrugged again. "It's okay. I don't like her _that_ much. I don't even know her."

Cas nodded in understanding. He studied Dean's face for a few moments, trying to decide if he was going too far by asking what he wanted to ask next. Maybe the alcohol was giving him confidence, or maybe it was making him stupid, because before his brain could catch up, he was already talking. "Can I ask _you_ something personal now?"

Dean turned his head from where he was staring off into space to focus his eyes on Cas'. "Sure."

Cas just stared back, feeling himself deflating as he lost his nerve. "Um..." He swallowed nervously. "Nevermind."

Dean grinned and shook his head. "No, no, no. Too late for that. Ask me."

Cas sighed and lowered his eyes. "Are you a virgin?"

Dean snorted a little laugh. "Nope." He paused. "I've only done it once though." He paused again, studying Cas' face as he continued to stare down at the bottle. "Are you?"

Without raising his eyes, Cas nodded.

"Damn man, that sucks. But you're only thirteen, so, you've got time."

Cas grimaced. "Don't remind me."

"What? There's nothing wrong with being thirteen. I'm only older because I'm stupid and got held back in fifth grade."

Cas finally looked up and squinted at him. "I don't think you're stupid."

Dean laughed. "Well, thanks, but my teachers would disagree with you."

They were quiet for a moment, until Cas asked another question. "So, what was it like?"

"What, being held back?"

"No..." Cas trailed off as his face flushed pink. "Having sex."

"Oh," Dean chuckled. "It was okay. Better than jerking off obviously, but I dunno. She just sorta laid there." He paused, worrying his bottom lip between his teeth before letting it pop back out. "Maybe I wasn't doing it right." He shook his head. "But she was a virgin, too, so I guess she wouldn't have known the difference, huh?" He laughed a little, but he looked embarrassed.

"What happened after?" Cas asked quietly.

Dean shrugged. "Nothing. We didn't really even like each other like that, really... We were just curious." He paused. "It was over the summer. She waves at me in the hallways sometimes but that's it."

Cas handed the bottle to Dean and sighed. "I don't think I will find anybody willing to experiment with me like that," he admitted. "Not around here."

"What do you mean?" Dean asked, quirking an eyebrow.

"This area seems very... conservative," he mumbled.

Dean shrugged, rolling the bottle between his palms and staring down at it. "You'd be surprised."

Cas raised his eyebrows, but he didn't say anything. Dean took another swig from the bottle, and Cas' eyes widened as he realized the amount they'd drank. Dean had certainly drank more, but they'd put an impressive dent in the bottle.

"Are you hungry?"

Dean lowered the bottle and swallowed down the liquid. "Yeah, actually."

Cas pushed himself up from the ground and stood up, leaning over and grabbing onto his desk for balance. He didn't realize how drunk he was until he stood up. He made his way to the bedroom door, turning in time to see Dean staggering up behind him.

They went down the hallway, Dean leaning on the wall, and stopped at the top of the stairs.

"Hold on to the railing, Dean," Cas warned.

"Yeah, yeah," Dean mumbled, but there was a smile in his voice. He grabbed onto the railing and took the first step, and Cas followed him down. Once they got into the kitchen, Cas flicked the light on.

"What do you want?"

"Oh, uh... whatever you 'ave is fine," Dean slurred, squinting into the light.

Cas tilted his head. "Well... I have a lot. So take your pick." He waved his hand towards the fridge. "The pantry is over there." He pointed to a door on the other end of the kitchen.

Dean's head was suddenly swimming from the walk down the stairs and the fluorescent lights of the kitchen. "Actu'ly, uh, d'you have crackers?"

Cas nodded and shuffled over to the pantry, opening the door and rummaging around. He closed the door and came back with a roll of Ritz crackers. "Here." He held them out.

Dean took them and quickly tore them open. "Thanks." He shoved two into his mouth, chewing and swallowing before clearing his throat. "So... where're your parents?"

"Work."

"It's almost midnight," Dean realized aloud.

Cas nodded. "Yeah. They go away for work. Usually for a week or two."

Dean's eyes nearly bugged out of his head and he choked on his most recent cracker. He coughed for a moment, and when he finally cleared his throat, he gawked, "Your parents leave you alone for that long?"

Cas nodded. "Yes."

"Damn, man, you should 'ave parties here."

Cas' brows knitted together in confusion. "Who would I invite?"

Dean thought for a moment. "Good point. Guess it'll jus' have to be us."

Cas smiled. "I would like that." He observed Dean eat for a moment before clearing his throat. "Do you want to go back upstairs? We can watch TV. Or, uh, play the game s'more."

Dean nodded. "Okay. TV sounds good. I'm prob'ly too drunk to play."

They went back upstairs and sat cross-legged on the bed. They watched two episodes of Family Guy before Dean leaned over and set the remainder of the bottle on Cas' desk. He turned back to the TV, but his eyes kept falling closed.

"Um... I'm gonna go outside," he mumbled, pushing himself off the bed. "Have a cig'rette."

"You can smoke in here," Cas said, eyeing him as he stumbled off the bed. "I'm not sure you should go down the stairs."

"...Y'sure?"

Cas nodded. "It's okay."

Dean reached down and rummaged through the pockets of his jacket, which was lying on the floor by the bed. He located a pack of cigarettes and a lighter, and then his eyes swept the room before settling on a soda can on the desk. He reached out and grabbed it, holding it up. "Is this empty?"

Cas nodded. "Yes. You can ash in it."

Dean nodded and sat back down on the bed, crossing his legs and settling it in the little V in front of his crotch. He shook a cigarette out of the pack and lit it up, closing his eyes and inhaling deeply.

Cas watched his lips wrap around the filter, watched the way his cheeks hollowed as he pulled, watched his lips part as he released the smoke. He felt his dick stirring to life in his pants, and he had to look away.

"Want some?"

He looked back to see Dean staring at him and holding out the cigarette. "Sure." He took it from him and brought it to his lips, taking a small pull. He pulled the cigarette away and sucked in a bit of air, and as soon as the smoke hit his lungs he felt like he'd been punched. The smoke poured out in a fit of coughs, and his eyes began watering as his free hand came up to smack his palm into his chest.

Besides him, Dean was laughing. "It gets smoother."

Cas nodded, sucking in a breath of fresh air and catching his breath before trying again. This time he knew what to expect, and he only let out one small cough on the exhale.

"There ya go," Dean said with a nod, taking his cigarette back.

Cas smiled over at him. "You're a bad influence," he said, his voice a bit strained from the coughing.

"Yeah," Dean chuckled, "I am." He squinted across the room at the cable box below Cas' TV. It was almost one. "We should probably go to sleep," he said through a yawn. "I gotta get home in the mornin' an' feed Sammy." He took another drag off his cigarette and ashed it into the can.

Cas nodded. "You can sleep up here if you want. I can sleep on the floor."

Dean raised an eyebrow. "Why would you sleep on the floor?"

Cas shrugged, looking away. "I don't know. I guess I figured you wouldn't want to share a bed after, y'know-"

"Findin' out you're gay?" Dean snorted a laugh. "I'm not like that, dude."

Relief washed over Cas' face and he nodded. Then he stood up, swaying slightly. "I'm going to get changed." He crossed the room to his dresser and pulled out a pair of pajama pants. As he crossed the room again, towards the door, he stopped in his tracks when Dean spoke.

"Dude, I've seen you change in the locker room before. You don't haveta go in the bathroom."

Cas turned around. "Right." He wasn't sure why, but he felt like this was different. He fumbled with his belt buckle for a moment until it popped open. His pants fell, pooling around his ankles and leaving him in just his boxers and tee shirt. He stepped out of them and pulled the pajama pants on, nearly losing his balance and falling over but catching himself at the last second.

He rounded the bed and pulled the covers back, sitting down and pushing his legs underneath.

"Um... I actu'ly forgot pajamas," Dean mumbled, staring down at his cigarette. "Is it okay if I sleep in boxers 'n' a shirt?"

Cas nodded. "Of course. I don't care."

"Thanks," Dean said quietly. He took one last drag off of cigarette and dropped the end in the can. It hissed as it was extinguished in the remaining liquid, and he reached over and deposited it on the desk. He leaned back and undid his belt, popping his jeans open and shimmying them down. He tossed them to the floor and pushed the blanket down, tucking his legs beneath it before yanking it back up.

"Your bed is super comfy," he slurred, reaching over again for the liquor bottle. He tilted it back and took another large swallow before setting it down again.

Cas wasn't sure what the point was of drinking more if they were about to go to sleep, but he didn't ask. Dean seemed to be more experienced than he was when it came to drinking.

"Mine sucks," he continued, lying on his back and closing his eyes. "An' it's small. Yours is huge."

"Thank you," Cas said quietly. He reached out and turned off the lamp on his nightstand, shrouding the room in darkness. "Goodnight, Dean."

"Night, Cas."

Cas leaned back and settled down into the pillows, rolling over onto his side to face the window. A few minutes passed, and he was just dozing off when Dean spoke next to him, his voice heavy and thick with intoxication.

"Hey, Cas?"

"Yes?"

"How- how'd you know you were gay?" Dean slurred.

Cas lifted his head, unsure if he heard him correctly. "Excuse me?"

"How'd you know?" Dean repeated.

"Well... I don't find girls attractive," he said into the darkness, settling his head back down into the pillow.

"Oh," Dean said softly. He liked girls, so he guessed he really wasn't gay. Was it possible to like both? Dean was quiet for another minute or so, and Cas figured he'd finally passed out, until he started talking _again_. "I know you said- you said yer a virgin," he slurred, and Cas was having a hard time understanding him. "But you've never done _anythin'_?"

"No," Cas admitted.

"D-d'you wanna?"

"What?" Cas asked, squinting into the darkness. Of course he wanted to, he was almost fourteen. He felt Dean shifting, and then a warm hand was placed on his waist. He immediately stiffened, and he suddenly felt Dean's warm breath on his neck. "Dean, what're you-"

"I'll es- I'll esperiment with you, Cas," Dean said softly.

Cas' dick immediately began responding in his pants, and his heart kicked into overdrive, hammering in his chest. "Dean, you're drunk," he said shakily. He wasn't ready for this. He wasn't ready to full-on have sex.

"I know," Dean admitted. "Sorry."

"You don't have to be sorry, Dean," Cas said softly. "I just don't want you doing somethin' you regret." He paused, chewing his lip. "You said you like girls."

"Girls ain't that great," he murmured, sliding his hand forward to rest on Cas' stomach.

Cas placed his hand on Dean's to stop it from moving. "Dean, you're drunk," he repeated. It was all he could think to say, his head swimming in confusion and mild intoxication.

Dean wriggled his fingers until they popped between Cas', effectively lacing them together. "If you wan' me to stop... I'll roll over ri' now," he slurred in Cas' ear.

His warm breath on his ear sent a shiver down Cas' spine. "I... I'm not saying that," he said quietly. "I- I'm just..." He swallowed hard and let out a deep sigh. As much as he wanted it, he just wasn't ready. "I'm just not ready to have sex."

"I wasn't talkin' 'bout that," Dean said. "There's so much more... we can do... We don' even haveta take our clothes off."

Cas turned his head to look at Dean, although he could only see his silhouette in the dark. "...Really?"

Dean huffed a laugh, and the smell of whiskey washed over Cas' face. "Yeah. ...You wanna?"

Cas sucked in a sharp breath and closed his eyes. "...Yes."

Dean's fingers tightened on Cas'. "If you wan' me to stop, you say stop. 'Kay?"

Cas audibly swallowed. "Okay."

Dean leaned forward and lightly pressed their lips together, soft and gentle. At first, Cas wasn't sure what to do, but once his brain got with the program he moved his mouth as well. He felt Dean's tongue swipe over his lower lip, so he parted them, and then Dean's tongue was inside. He tasted like whiskey and cigarettes and something else Cas couldn't place, and he _loved_ it. A small groan escaped from his throat, and Dean swallowed it down.

Dean wiggled his fingers, so Cas moved his hand, and Dean slid his down to graze them over Cas' hardening member through his pajamas. When it earned him a soft moan, he cupped him in his hand, giving him a gentle squeeze.

Cas broke away from the kiss. "Shit," he huffed.

Suddenly Dean pulled his hand away and Cas was momentarily disappointed, his hips twitching a bit at the loss of contact. But then Dean was pushing himself up, swinging one leg over Cas' hip and settling down on top of him. Dean leaned forward and took Cas' face in his hands, his fingers resting on his neck and his thumbs on his jawline. A small gasp escaped Cas as he felt Dean's erection slotted alongside his own.

Dean leaned down and kissed him again, and this time Cas was ready. He pushed his own tongue inside Dean's mouth before Dean got a chance to do it to him, and Dean emitted a startled groan into Cas' mouth in response. He slowly rutted his hips down, and that was too much for Cas. He broke the kiss to crane his head back, moaning loudly.

"Dean... oh my god," he groaned.

"I know," Dean slurred, pressing his lips to Cas' exposed throat. He rolled his hips again, enjoying the vibration of Cas' throat on his mouth as he pulled another moan out of him. He dragged his mouth along his neck, occasionally flicking his tongue out to lick the soft skin there.

Cas twitched his hips up into Dean, feeling the warmth of his hard cock through the thin material of his boxers.

"Ugh," Dean grunted, burying his face in Cas' neck. "You're good a' this."

Cas huffed a laugh, rolling his hips up again. "Thank you," he breathed. He could feel the heat pooling in his belly already, and he tried to stave it off, but then Dean thrust his hips downward again onto him, and he felt everything tightening as he neared release. "Dean-"

Dean cut him off by lifting his head and sealing their lips together again. He suddenly dropped down onto his elbows, framing Cas' face with his forearms, and threaded his fingers through his hair as they kissed with urgency. Dean kept thrusting downward, grinding their dicks together, as Cas squirmed beneath him.

It was only another minute or less of rutting against each other before Cas stiffened, breaking the kiss to turn his head and squeeze his eyes shut as his release slammed out of him and into his boxers with a long, low moan. Dean followed soon after, tightening his grip in Cas' hair so hard it almost hurt, grunting through gritted teeth as he came between them.

They stilled for a few moments, huffing and panting, before Dean straightened up and looked down at Cas' silhouette. "Was..." He huffed a breath and swallowed. "Was tha'- did you like it?"

"Yes," Cas breathed, staring up at the dark ceiling. "Fuck... yes."

Dean huffed a laugh, rolling off of him and flopping onto his back. Cas listened to him panting for a moment, trying to calm his own heart, which was hammering against his rib cage.

"Thank you," he finally said.

"You're... welcome," Dean murmured.

They laid there quietly for a few minutes, until Cas cleared his throat. "Dean?"

"Hmm?"

"You should come over more often."

Dean snorted a drunken laugh. "I agree," he mumbled.

Within a minute Dean was snoring, leaving Cas staring up at the ceiling. He couldn't believe he just had his first sexual experience, and with _Dean_ , no less. He liked Dean a lot, and he just hoped Dean wasn't going to wake up in the morning and be embarrassed, or regret what they'd done. He shifted to roll over, and grimaced when he felt the cold sticky come in his pajamas. He lifted the blanket and climbed out of bed, grabbing clean boxers and pajamas from his dresser and padding across the bedroom to the door. He went down the hallway and into the bathroom and stripped down, then cleaned up with a wet washcloth and got re-dressed.

He stared at himself in the mirror for a few minutes. His hair was a mess, his cheeks were pink, and his lips were red and spit-slicked. While he didn't look any different aside from that, he certainly _felt_ different. What he and Dean just did was amazing, and he wanted more. So much more.

Once he got back into the bedroom, he tossed the soiled clothes and washcloth into the laundry basket and slid back under the covers. With the sound of Dean snoring next to him and post-orgasm drowsiness washing over him, he closed his eyes and slipped off to sleep within minutes.

* * *

When Dean awoke the next morning, he was shocked to find himself spooning up behind Cas, one arm thrown over his waist. He immediately stiffened and recoiled his hand, scooting back to the edge of the bed. Once he realized Cas was still asleep, he let out a small sigh of relief. Thank god Cas hadn't woken up- he would've been totally weirded out and probably never invited Dean over again.

He shifted to lie on his back and grimaced in pain when he felt dried come pulling on his pubes. _Fuck._ He briefly remembered rutting up against Cas. He must've had a wet dream. Jesus, that's embarrassing. God, what if he humped the guy in his sleep? That probably didn't happen, but what if Cas heard him moaning in his sleep or something? Dean tried to tell himself he probably would've kicked him out of the bed if that was the case.

He got _way_ too drunk last night. He couldn't even remember anything. Suddenly, Cas stirred next to him. Dean immediately stiffened and Cas rolled over, blinking his eyes open and giving him a sleepy smile.

"Good morning."

Dean smiled sheepishly. "'Mornin'."

Cas brought a fist up to rub the sleep from his eyes. "Breakfast?"

"Uh, yeah," Dean agreed. "Sounds good." He paused, watching as Cas blinked blearily. "Um, listen, I'm sorry I got so drunk last night."

Cas gave him a grin. "It's okay."

Dean frowned at him. "I hope I didn't do anything stupid."

Cas' eyebrows knitted together. "Uh... no. You didn't." He studied Dean's face for a moment. "...Do you remember anything?"

Dean's forehead momentarily creased in thought before smoothing out as he shook his head slightly. "Last thing I remember is eating crackers in the kitchen. And I think we watched some Family Guy...?"

Cas frowned. "Uh... yeah."

Dean shifted uncomfortably. "This is really fucking awkward, but do you think I could take a shower? I kind of, um... had a dream," he admitted, looking away. "About Lisa," he added quickly. He wasn't about to admit that he had a wet dream about Cas. No way in hell.

Cas was glad Dean was facing away so he didn't see the disappointment on his face. Did Dean think he was Lisa last night? Fuck, he felt so stupid. He knew Dean was straight. Why the hell did he allow himself to believe anything different?

He cleared his throat and threw the covers back, pushing himself out of bed. "Yeah. Come with me." He crossed the room, and he could sense Dean following behind him. He went into the bathroom and turned on the water, and Dean had to keep his eyes to the floor to avoid staring at his ass.

Cas straightened up and turned around. "I'll get you a towel." He left and momentarily returned with a towel and washcloth, setting them on the counter. "I'm going to make breakfast," he said, avoiding Dean's eyes. "Just come down when you're done."

Dean nodded. "Thanks." Cas turned and left, closing the door behind him.

Dean dropped his head into his hands and groaned. The dream kept replaying in his head, and his dick was already responding. He was so screwed. He sighed and turned around, dropping his boxers and pulling his shirt off over his head. He stepped into the bathtub, letting the hot water wash over him. He tilted his head back and opened his mouth, willing the water to flood his lungs and just drown him now.

But survival skills be damned, his throat wouldn't open up and betray him. He looked down at his half-hard dick, and suddenly an image of Cas on his knees sucking him off flashed through his mind. He groaned in frustration as he began to swell further. No use trying to fight it now. He might as well jack off really quick, otherwise he might be fighting this boner all throughout breakfast.

He reached down and took himself in his hand, his lips parting and his eyes falling closed. He slowly stroked upwards- once, twice, and then his mind flashed back to the dream. They'd still been in their clothes, and now that he thought about it, it seemed like such a waste of a perfectly good wet dream. He was awake now, and he could imagine whatever he wanted.

He pictured pushing both of their boxers down, taking both of them in hand and jerking them together. He moved his hand up and down slowly as he imagined kissing Cas' soft lips, swallowing down his moans as precome leaked from both of them. He spread it around with his thumb, jerking a little rougher as Cas pushed his tongue into his mouth.

In the shower, he jerked his wrist a little faster, biting his lip to stifle any moans trying to escape his throat.

He pictured Cas breaking the kiss to tilt his head and latch onto Dean's neck, sucking dark marks into his skin to claim him as his own. _Property of Castiel._ He wasn't sure where the hell that came from, but as he rutted up against imaginary Cas, their cocks sliding together and sticky with precome, he let out a low groan, his hips twitching as he blew his load all over the tiled shower wall.

He re-opened his eyes and let his lip pop out from between his teeth, looking down at the streaks of white on the tile. Suddenly he felt guilty and _wrong_ , and even though his legs were shaking a bit, he quickly reached up and detached the shower head, turning it to rinse his release away.

He sucked in a breath, and suddenly every homophobic thing his father had ever said flooded his brain. He felt bile rising in the back of his throat, but he swallowed it down. Thoughts were one thing. As long as he didn't act on it, he wasn't gay. _He wasn't gay._

He washed up as quickly as possible and got re-dressed, folding his soiled boxers as flat as possible and tucking them into his jacket pocket. When he made his way downstairs, Cas was already sitting at the table, poking at a plate of eggs. Across from him was a second plate, piled with eggs and bacon.

Dean crossed the room and lowered himself into the seat, picking up his fork and poking at his eggs as well. "Thank you," he said quietly.

"No problem," Cas said, keeping his voice even. He'd had time to even himself out while Dean was in the shower. He didn't want Dean to think Cas was acting weird simply because he'd had a wet dream.

"I'm really sorry I violated your bed," Dean mumbled.

Cas snorted a laugh. "Stop it, Dean. You didn't violate my bed. It happens." He glanced up, and Dean was staring at him with a frown, so he offered him a reassuring smile. "Really. It's okay."

Dean swallowed and nodded, turning his attention to his plate. He picked up a piece of bacon and took a bite, munching on it as Cas ate his eggs. Once they finished, he glanced up at the clock on the wall and saw that it was already nine.

"Shit, I have to go check on Sammy."

Cas nodded. "Thank you for coming over."

"Thanks for having me, Cas, really. I had fun. I hope we can do it again soon."

Cas smiled. "I would like that." Dean stood up and Cas started to get up as well. "Let me walk you out."

"No, it's okay," Dean said quickly. "Finish your breakfast. I'll see you Monday."

Cas sat back down and nodded. "Okay. See you Monday."

Dean offered him a smile, then turned and headed for the door. As it closed behind him, Cas was left alone again, for the rest of the weekend. He stared down at his plate and let out a heavy sigh, vowing that he would never tell Dean about what they'd done. It just wasn't worth losing him as a friend.

**Notes for the Chapter:**

> Please let me know what you thought! <3


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